ES2623495T3 - Procedure for the preparation of a thioprecursor for statins - Google Patents

Procedure for the preparation of a thioprecursor for statins Download PDF

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Publication number
ES2623495T3
ES2623495T3 ES12795483.2T ES12795483T ES2623495T3 ES 2623495 T3 ES2623495 T3 ES 2623495T3 ES 12795483 T ES12795483 T ES 12795483T ES 2623495 T3 ES2623495 T3 ES 2623495T3
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ES
Spain
Prior art keywords
carbon atoms
general formula
compound
preparation
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
ES12795483.2T
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Spanish (es)
Inventor
De Ben Lange
Dennis Heemskerk
Karin Henderika Maria BESSEMBINDER
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Centrient Pharmaceuticals Netherlands BV
Original Assignee
DSM Sinochem Pharmaceuticals Netherlands BV
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Application filed by DSM Sinochem Pharmaceuticals Netherlands BV filed Critical DSM Sinochem Pharmaceuticals Netherlands BV
Application granted granted Critical
Publication of ES2623495T3 publication Critical patent/ES2623495T3/en
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Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Un método para la preparación de un compuesto de fórmula general (2)**Fórmula** donde R2 y R3 representan cada uno independientemente un alquilo de 1 a 12 átomos de carbono, un alquenilo de 1 a 12 átomos de carbono, un cicloalquilo de 3 a 7 átomos de carbono, a cicloalquenilo de 3 a 7 átomos de carbono, un arilo de 6 a 10 átomos de carbono o un aralquilo de 7 a 12 átomos de carbono, donde cada uno de R2 y R3 puede estar substituido y donde R2 10 y R3 pueden formar un anillo junto con el átomo de carbono al que están unidos, y donde R4 es un grupo alquilo o alquenilo de 1 a 6 átomos de carbono, y donde R5 es un grupo arilo, consistente en las siguientes etapas: (a) mezclar un compuesto de fórmula general R5-SH con una base; (b) añadir a la mezcla obtenida en la etapa (a) agua y un compuesto de fórmula general (4)**Fórmula** donde X es halógeno; (c) añadir durante y/o después de la etapa (b) un alcohol de fórmula general R4-OH; (d) añadir un acetal o un alcoxialqueno o una cetona y eliminar el agua antes de, durante o después de dicha adición; (e) añadir un ácido a la mezcla obtenida en la etapa (c) y/o en la etapa (d).A method for the preparation of a compound of the general formula (2)**Formula** where R2 and R3 each independently represent an alkyl of 1 to 12 carbon atoms, an alkenyl of 1 to 12 carbon atoms, a cycloalkyl of 3 to 7 carbon atoms, to cycloalkenyl of 3 to 7 carbon atoms, an aryl of 6 to 10 carbon atoms, or an aralkyl of 7 to 12 carbon atoms, where each of R2 and R3 may be substituted and where R2 10 and R3 can form a ring together with the carbon atom to which they are attached, and where R4 is an alkyl or alkenyl group of 1 to 6 carbon atoms, and where R5 is an aryl group, consisting of the following steps: ( a) mixing a compound of the general formula R5-SH with a base; (b) adding to the mixture obtained in step (a) water and a compound of general formula (4)**Formula** where X is halogen; (c) adding during and/or after step (b) an alcohol of the general formula R4-OH; (d) adding an acetal or an alkoxyalkene or a ketone and removing water before, during or after said addition; (e) adding an acid to the mixture obtained in step (c) and/or in step (d).

Description

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Claims (1)

imagen1image 1
ES12795483.2T 2011-12-09 2012-12-06 Procedure for the preparation of a thioprecursor for statins Active ES2623495T3 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP11192749 2011-12-09
EP11192749 2011-12-09
PCT/EP2012/074689 WO2013083719A1 (en) 2011-12-09 2012-12-06 Process for the preparation of a thioprecursor for statins

Publications (1)

Publication Number Publication Date
ES2623495T3 true ES2623495T3 (en) 2017-07-11

Family

ID=47291022

Family Applications (1)

Application Number Title Priority Date Filing Date
ES12795483.2T Active ES2623495T3 (en) 2011-12-09 2012-12-06 Procedure for the preparation of a thioprecursor for statins

Country Status (10)

Country Link
US (1) US9260423B2 (en)
EP (1) EP2788341B1 (en)
CN (1) CN103987705B (en)
ES (1) ES2623495T3 (en)
HK (1) HK1201063A1 (en)
HU (1) HUE032936T2 (en)
IL (1) IL232804A (en)
MX (1) MX363563B (en)
SI (1) SI2788341T1 (en)
WO (1) WO2013083719A1 (en)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2294236T3 (en) 1998-08-05 2008-04-01 Kaneka Corporation PROCEDURE FOR THE PREPARATION OF ESTERES REPLACED WITH 3,5-DIHIDROXI AS INTERMEDIATES TO PRODUCE ACID DERIVATIVES 2- (6-HIXIMETIL) -1,3-DIOXAN-4-IL) OPTICALLY ACTIVE ACETIC.
GB9903472D0 (en) 1999-02-17 1999-04-07 Zeneca Ltd Chemical process
US20020028826A1 (en) 2000-06-15 2002-03-07 Robl Jeffrey A. HMG-CoA reductase inhibitors and method
NL1015744C2 (en) * 2000-07-19 2002-01-22 Dsm Nv Process for the preparation of 2- (6-substituted-1,3-dioxan-4-yl) acetic acid derivatives.
MXPA03011195A (en) * 2001-06-06 2004-03-18 Bristol Myers Squibb Co Process for preparing chiral diol sulfones and dihydroxy acid hmg coa reductase inhibitors.
DK1404844T3 (en) 2001-07-12 2007-06-04 Dsm Ip Assets Bv Process for Preparation of 2,4-Dideoxy Hexoses and 2,4,6-Trideoxy Hyxoses
CZ299215B6 (en) 2005-06-29 2008-05-21 Zentiva, A. S. Process for preparing hemi-calcium salt of rosuvastatin, i.e. (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxy-6-heptenoic acid

Also Published As

Publication number Publication date
EP2788341A1 (en) 2014-10-15
HUE032936T2 (en) 2017-11-28
EP2788341B1 (en) 2017-04-05
IL232804A0 (en) 2014-08-03
CN103987705B (en) 2015-09-30
CN103987705A (en) 2014-08-13
IL232804A (en) 2017-01-31
HK1201063A1 (en) 2015-08-21
MX2014006893A (en) 2014-09-04
US20140343292A1 (en) 2014-11-20
US9260423B2 (en) 2016-02-16
MX363563B (en) 2019-03-27
WO2013083719A1 (en) 2013-06-13
SI2788341T1 (en) 2017-06-30

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